As wonderful a thing as an overdrive transmission is, it only affects the compound high gear. In your case, you made a significant change in compound high, going from a 3.73 to a 2.41. An overdrive will not suddenly give you some "Great leap forward" in highway fuel economy beyond that which you would get by going to the same rear gear ratio as the compound ratio you would get from an overdrive. For example, if you ran a TH 200 4R with the 3.73, 3.73 X 0.67=2.49, or only slightly higher than you have now. At a steady state highway speed, this is all that really matters. Yes, you can over do gears and drop fuel economy, but I tend to think that is not the case here. Also, if you do a lot of stop and go during the trip, the 2.41 will adversely affect the fuel economy ( as will the Edelbrock carb vs a Q-Jet) since wheel torque per throttle opening percentage will be lessened. One thing you didn't say is if you are running a vacuum advance on your distributor. Not having it hooked up will negatively affect fuel economy too. I will also say that a change in fuel formulation may be affecting it too. The EPA is mandating more ethanol as an oxygenating agent in some places, and this can lead to a drop in fuel mileage. I have noticed this in my local area over the last year or so as both my running cars have lost a significant amount of fuel mileage due to the reformulation of local gas supplies. Why is this so? Well, ethanol has significantly fewer BTU's of energy per given volume of fuel, thus requiring the use of more fuel to achieve similar power levels. Remember that the stoichiometric mix of normal gas to air is 14.7:1 while ethanol requires a much richer 9.9:1 mix.
My gearing right now is a 3.23 with the TH 200 4R overdrive. The compound high is 2.14:1. This lets me have the better gearing to get me off the line with less throttle input in traffic, but still lets me have reasonable steady state fuel economy too. My engine is set to have a torque curve that begins in earnest around 1800 RPM, so it is about ideal for my situation. However, I do wish I had a manual transmission because I can see where the converter slippage hurts things on the tach. As for the rest of the combo, most of it is tuned for fuel economy. The Quadrajet is like having a 200 CFM 2 barrel almost all of the time. The secondaries do not come in to play until you really step on it. The same is true of your Edelbrock, but it drives like a 300 CFM 2 barrel most of the time because it is a square flange carb. What is the difference? Well, the smaller venturis in the Q-Jet have a stronger vacuum signal at a lower RPM and can thus run a slower idle speed. They also make the engine more efficient as they produce more torque at part throttle than a bigger carb can.